EP0695759A3 - Human cancer inhibitory pentapeptide methyl esters - Google Patents

Human cancer inhibitory pentapeptide methyl esters Download PDF

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Publication number
EP0695759A3
EP0695759A3 EP95305130A EP95305130A EP0695759A3 EP 0695759 A3 EP0695759 A3 EP 0695759A3 EP 95305130 A EP95305130 A EP 95305130A EP 95305130 A EP95305130 A EP 95305130A EP 0695759 A3 EP0695759 A3 EP 0695759A3
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EP
European Patent Office
Prior art keywords
cbz
chem
methyl esters
human cancer
cancer inhibitory
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP95305130A
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German (de)
French (fr)
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EP0695759B1 (en
EP0695759A2 (en
Inventor
George R. Pettit
Michael D. Williams
Jayaram K. Srirangam
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University of Arizona
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University of Arizona
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Publication of EP0695759A2 publication Critical patent/EP0695759A2/en
Publication of EP0695759A3 publication Critical patent/EP0695759A3/en
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Publication of EP0695759B1 publication Critical patent/EP0695759B1/en
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Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Herein disclosed are several pentapeptide methyl ester derivatives of dolastatin 10, using both naturally occurring and modified amino acids. The selected modified amino acids are constituents of dolastatin 10 which is a structurally distinct peptide with excellent in vitro and in vivo antineoplastic activity. The structures of these compounds are as shown below: <MATH> 10a) R1 = i-Pr ; R = -NH(Me)2 ; R2 = -CH2CH2CH2NH-cbz 10b) R1 = i-Pr ; R = -NH (Me)2 ; <CHEM> 11a) R1 = - (CH2)4NH-cbz ; R = -NH (cbz) ; <CHEM> 11b) <CHEM> R = -NH(cbz) ; R2 = -CH2CH2CH2NH-cbz 11c) <CHEM> R = -NH(cbz) ; R2 = -CH2-S-Me m
EP95305130A 1994-08-01 1995-07-21 Human cancer inhibitory pentapeptide methyl esters Expired - Lifetime EP0695759B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US283682 1994-08-01
US08/283,682 US5504191A (en) 1994-08-01 1994-08-01 Human cancer inhibitory pentapeptide methyl esters

Publications (3)

Publication Number Publication Date
EP0695759A2 EP0695759A2 (en) 1996-02-07
EP0695759A3 true EP0695759A3 (en) 1997-11-26
EP0695759B1 EP0695759B1 (en) 2002-05-22

Family

ID=23087105

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95305130A Expired - Lifetime EP0695759B1 (en) 1994-08-01 1995-07-21 Human cancer inhibitory pentapeptide methyl esters

Country Status (9)

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US (1) US5504191A (en)
EP (1) EP0695759B1 (en)
JP (1) JP3579750B2 (en)
AT (1) ATE217884T1 (en)
CA (1) CA2154203A1 (en)
DE (1) DE69526757T2 (en)
DK (1) DK0695759T3 (en)
ES (1) ES2176286T3 (en)
PT (1) PT695759E (en)

Families Citing this family (161)

* Cited by examiner, † Cited by third party
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EP0695759B1 (en) 2002-05-22
ATE217884T1 (en) 2002-06-15
US5504191A (en) 1996-04-02
CA2154203A1 (en) 1996-02-02
DK0695759T3 (en) 2002-07-29
ES2176286T3 (en) 2002-12-01
DE69526757T2 (en) 2002-11-07
DE69526757D1 (en) 2002-06-27
JP3579750B2 (en) 2004-10-20
EP0695759A2 (en) 1996-02-07
PT695759E (en) 2002-09-30
JPH0859693A (en) 1996-03-05

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